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J Org Chem

Title:		Synthesis and use of deuterated palmitic acids to decipher the cryptoregiochemistry of a Delta13 desaturation
Author(s):		Abad JL; Serra M; Camps F; Fabrias G;
Address:		"Departamento de Quimica OrgAnica Biologica, Instituto de Investigaciones Quimicas y Ambientales de Barcelona, Consejo Superior de Investigaciones Cientificas, J. Girona 18, 08034, Barcelona, Spain. jlaqob@iiqab.csic.es"
Journal Title:		J Org Chem
Year:		2007
Volume:		72
Issue:		3
Page Number:		760 - 764
DOI:		10.1021/jo061592s
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"The synthesis of two hexadeuterated palmitic acids differing in the position of the diagnostic labels, and their use to decipher the cryptoregiochemistry of a Delta13 desaturation are described. A dithiane and a triple bond functionalities were used to introduce the diagnostic (C13 or C14) and tagging (C8 and C9) labels, respectively, in the palmitic acid skeleton. Using these probes, the cryptoregiochemistry of the Delta13 desaturation involved in the biosynthesis of Thaumetopoea pityocampa sex pheromone was studied by means of kinetic isotope effect determinations. Transformation of both (Z)-11-hexadecenoic and 11-hexadecynoic acids into (Z, Z)-11,13-hexadecadienoic and (Z)-13-hexadecen-11-ynoic acids, respectively, is initiated by abstraction of the hydrogen atom at the C13 position, followed by the fast elimination of the C14 hydrogen to give the double bond"
Keywords:		"Animals Deuterium/*chemistry Fatty Acid Desaturases/*chemistry Isotopes/chemistry Kinetics Models, Chemical Moths/physiology Palmitic Acids/*chemical synthesis/chemistry Sex Attractants/biosynthesis/chemistry Stereoisomerism;"
Notes:		"MedlineAbad, Jose-Luis Serra, Montserrat Camps, Francisco Fabrias, Gemma eng Research Support, Non-U.S. Gov't 2007/01/27 J Org Chem. 2007 Feb 2; 72(3):760-4. doi: 10.1021/jo061592s"